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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:15 UTC

Update Date

2021-09-14 15:20:33 UTC

HMDB ID

HMDB0013861

Secondary Accession Numbers

HMDB13861

Metabolite Identification

Common Name

4-Hydroxyifosfamide

Description

4-Hydroxyifosfamide is the active metabolite of the bifunctional alkylating cytostatic drug known as ifosfamide. 4-Hydroxyifosfamide is a member of the compound class known as oxazaphosphorines. Oxazaphosphorines are any saturated six-membered heterocycle containing three carbon atoms and one each of oxygen, nitrogen and phosphorus, especially one in which the phosphorus atom is linked to both the nitrogen and oxygen atoms. 4-Hydroxyifosfamide is very unstable in plasma and a stabilization procedure by adding citric acid has been developed (PMID: 9172103 ). 4-Hydroxyifosfamide is known to pass through the blood-brain barrier, and can reach cerebrospinal fluid concentrations that are almost as high as plasma concentrations (PMID: 9677448 ). 4-Hydroxyifosfamide is only found in individuals who have consumed or received the drug Ifosfamide.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0013861
     RDKit          3D
4-Hydroxyifosfamide
 30 30  0  0  0  0  0  0  0  0999 V2000
    0.7116   -0.9215   -1.7620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930   -0.7244   -0.3075 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.7883   -0.0684    0.5656 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9951   -0.2831   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1749    0.2551    0.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6726   -0.0105   -0.3925 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0896   -2.2358    0.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0772   -2.2014    1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2252   -1.7604    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2260   -0.2690    0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9864   -0.0169   -1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.3342   -0.0353 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653    1.5563   -0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    2.7358   -0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2813    2.5122    0.0960 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6538    0.9268    0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    0.2789   -1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1276   -1.3472   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0896    1.3252    0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689   -0.2750    1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986   -1.5569    2.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2792   -3.2354    1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1636   -2.0316    0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428   -2.3204   -0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8053    0.1639    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8938   -0.7939   -1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2308    1.8279   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2244    1.4721   -1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544    3.0580    0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    3.6055   -0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12  2  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
M  END

  Mrv0541 10041215372D          

 15 15  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000    2.2150    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  7  1  0  0  0  0
 14  6  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013861

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CCOP(=O)(NCCCl)N1CCCl

> <INCHI_IDENTIFIER>
InChI=1S/C7H15Cl2N2O3P/c8-2-4-10-15(13)11(5-3-9)7(12)1-6-14-15/h7,12H,1-6H2,(H,10,13)

> <INCHI_KEY>
JHUJMHKRHQPBRG-UHFFFAOYSA-N

> <FORMULA>
C7H15Cl2N2O3P

> <MOLECULAR_WEIGHT>
277.085

> <EXACT_MASS>
276.019734282

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.720144037331472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-4-hydroxy-1,3,2λ⁵-oxazaphosphinan-2-one

> <ALOGPS_LOGP>
-0.06

> <JCHEM_LOGP>
-0.05733287299999987

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.758644718366504

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.910527970292556

> <JCHEM_PKA_STRONGEST_BASIC>
-3.481640772688669

> <JCHEM_POLAR_SURFACE_AREA>
61.8

> <JCHEM_REFRACTIVITY>
59.09439999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxyifosfamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013861
     RDKit          3D
4-Hydroxyifosfamide
 30 30  0  0  0  0  0  0  0  0999 V2000
    0.7116   -0.9215   -1.7620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930   -0.7244   -0.3075 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.7883   -0.0684    0.5656 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9951   -0.2831   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1749    0.2551    0.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6726   -0.0105   -0.3925 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0896   -2.2358    0.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0772   -2.2014    1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2252   -1.7604    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2260   -0.2690    0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9864   -0.0169   -1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.3342   -0.0353 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653    1.5563   -0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    2.7358   -0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2813    2.5122    0.0960 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6538    0.9268    0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    0.2789   -1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1276   -1.3472   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0896    1.3252    0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689   -0.2750    1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986   -1.5569    2.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2792   -3.2354    1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1636   -2.0316    0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428   -2.3204   -0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8053    0.1639    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8938   -0.7939   -1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2308    1.8279   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2244    1.4721   -1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544    3.0580    0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    3.6055   -0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12  2  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
M  END

HEADER    PROTEIN                                 04-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM    9 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   10  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
CONECT    1    6    7                                                       
CONECT    2    4    8                                                       
CONECT    3    5    9                                                       
CONECT    4    2   10                                                       
CONECT    5    3   11                                                       
CONECT    6    1   14                                                       
CONECT    7    1   11   12                                                  
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4   15                                                       
CONECT   11    5    7   15                                                  
CONECT   12    7                                                            
CONECT   13   15                                                            
CONECT   14    6   15                                                       
CONECT   15   10   11   13   14                                             
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0013861
HETATM    1  O1  UNL     1       0.712  -0.921  -1.762  1.00  0.00           O  
HETATM    2  P1  UNL     1       0.393  -0.724  -0.307  1.00  0.00           P  
HETATM    3  N1  UNL     1       1.788  -0.068   0.566  1.00  0.00           N  
HETATM    4  C1  UNL     1       2.995  -0.283  -0.188  1.00  0.00           C  
HETATM    5  C2  UNL     1       4.175   0.255   0.562  1.00  0.00           C  
HETATM    6 CL1  UNL     1       5.673  -0.010  -0.393  1.00  0.00          CL  
HETATM    7  O2  UNL     1       0.090  -2.236   0.386  1.00  0.00           O  
HETATM    8  C3  UNL     1      -1.077  -2.201   1.150  1.00  0.00           C  
HETATM    9  C4  UNL     1      -2.225  -1.760   0.268  1.00  0.00           C  
HETATM   10  C5  UNL     1      -2.226  -0.269   0.046  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.986  -0.017  -1.117  1.00  0.00           O  
HETATM   12  N2  UNL     1      -0.935   0.334  -0.035  1.00  0.00           N  
HETATM   13  C6  UNL     1      -0.865   1.556  -0.761  1.00  0.00           C  
HETATM   14  C7  UNL     1      -1.541   2.736  -0.143  1.00  0.00           C  
HETATM   15 CL2  UNL     1      -3.281   2.512   0.096  1.00  0.00          CL  
HETATM   16  H1  UNL     1       1.654   0.927   0.816  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.936   0.279  -1.156  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.128  -1.347  -0.452  1.00  0.00           H  
HETATM   19  H4  UNL     1       4.090   1.325   0.751  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.269  -0.275   1.555  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.999  -1.557   2.038  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.279  -3.235   1.486  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.164  -2.032   0.806  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.143  -2.320  -0.699  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.805   0.164   0.887  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.894  -0.794  -1.718  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.231   1.828  -0.835  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.224   1.472  -1.810  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.054   3.058   0.816  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.433   3.605  -0.853  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7   12
CONECT    3    4   16
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    7    8
CONECT    8    9   21   22
CONECT    9   10   23   24
CONECT   10   11   12   25
CONECT   11   26
CONECT   12   13
CONECT   13   14   27   28
CONECT   14   15   29   30
END

HMDB0013861
     RDKit          3D
4-Hydroxyifosfamide
 30 30  0  0  0  0  0  0  0  0999 V2000
    0.7116   -0.9215   -1.7620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930   -0.7244   -0.3075 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.7883   -0.0684    0.5656 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9951   -0.2831   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1749    0.2551    0.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6726   -0.0105   -0.3925 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0896   -2.2358    0.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0772   -2.2014    1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2252   -1.7604    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2260   -0.2690    0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9864   -0.0169   -1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.3342   -0.0353 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653    1.5563   -0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    2.7358   -0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2813    2.5122    0.0960 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6538    0.9268    0.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    0.2789   -1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1276   -1.3472   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0896    1.3252    0.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689   -0.2750    1.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986   -1.5569    2.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2792   -3.2354    1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1636   -2.0316    0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428   -2.3204   -0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8053    0.1639    0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8938   -0.7939   -1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2308    1.8279   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2244    1.4721   -1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544    3.0580    0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    3.6055   -0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12  2  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-ifosfamide	HMDB
3-(2-Chloroethyl)-2-((2-chloroethyl)amino)-1,3,2-oxazaphosphinan-4-ol 2-oxide	HMDB

Chemical Formula

C₇H₁₅Cl₂N₂O₃P

Average Molecular Weight

277.085

Monoisotopic Molecular Weight

276.019734282

IUPAC Name

3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-4-hydroxy-1,3,2λ⁵-oxazaphosphinan-2-one

Traditional Name

4-hydroxyifosfamide

CAS Registry Number

67292-64-2

SMILES

OC1CCOP(=O)(NCCCl)N1CCCl

InChI Identifier

InChI=1S/C7H15Cl2N2O3P/c8-2-4-10-15(13)11(5-3-9)7(12)1-6-14-15/h7,12H,1-6H2,(H,10,13)

InChI Key

JHUJMHKRHQPBRG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isofamides. These are oxazaphospholanes containing the isofamide skeleton. Isofamide is a heterocyclic compound made up of a 1,3,2-oxazaphospholane, where the phosphorus atom is part of a phosphodiamide group, and the oxazaphospholane is substituted by two haloalkyl chains.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazaphosphinanes

Sub Class

Isofamides

Direct Parent

Isofamides

Alternative Parents

Substituents

Isofamide
Phosphoric monoester diamide
Organic phosphoric acid derivative
Organic phosphoric acid amide
Alkanolamine
Azacycle
Oxacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organic oxygen compound
Organohalogen compound
Organic nitrogen compound
Alkyl halide
Alkyl chloride
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ifosfamides (CHEBI:80560 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0013861)
Kidney (HMDB: HMDB0013861)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013861)

Source

Endogenous

Endogenous (HMDB: HMDB0013861)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Ifosfamide Action Pathway (PathBank: SMP0000448)

Metabolic pathway

Ifosfamide Metabolism Pathway (PathBank: SMP0000605)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	22.2 g/L	ALOGPS
logP	-0.06	ALOGPS
logP	-0.057	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	12.91	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.8 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	59.09 m³·mol⁻¹	ChemAxon
Polarizability	24.72 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	148.189	30932474
DeepCCS	[M-H]-	145.815	30932474
DeepCCS	[M-2H]-	181.121	30932474
DeepCCS	[M+Na]+	155.928	30932474
AllCCS	[M+H]+	155.8	32859911
AllCCS	[M+H-H2O]+	152.5	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.8	32859911
AllCCS	[M-H]-	152.9	32859911
AllCCS	[M+Na-2H]-	153.9	32859911
AllCCS	[M+HCOO]-	155.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyifosfamide	OC1CCOP(=O)(NCCCl)N1CCCl	3048.3	Standard polar	33892256
4-Hydroxyifosfamide	OC1CCOP(=O)(NCCCl)N1CCCl	2062.8	Standard non polar	33892256
4-Hydroxyifosfamide	OC1CCOP(=O)(NCCCl)N1CCCl	2161.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyifosfamide,1TMS,isomer #1	C[Si](C)(C)OC1CCOP(=O)(NCCCl)N1CCCl	2142.8	Semi standard non polar	33892256
4-Hydroxyifosfamide,1TMS,isomer #2	C[Si](C)(C)N(CCCl)P1(=O)OCCC(O)N1CCCl	2181.4	Semi standard non polar	33892256
4-Hydroxyifosfamide,2TMS,isomer #1	C[Si](C)(C)OC1CCOP(=O)(N(CCCl)[Si](C)(C)C)N1CCCl	2182.6	Semi standard non polar	33892256
4-Hydroxyifosfamide,2TMS,isomer #1	C[Si](C)(C)OC1CCOP(=O)(N(CCCl)[Si](C)(C)C)N1CCCl	2132.1	Standard non polar	33892256
4-Hydroxyifosfamide,2TMS,isomer #1	C[Si](C)(C)OC1CCOP(=O)(N(CCCl)[Si](C)(C)C)N1CCCl	2810.3	Standard polar	33892256
4-Hydroxyifosfamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CCOP(=O)(NCCCl)N1CCCl	2367.0	Semi standard non polar	33892256
4-Hydroxyifosfamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCC(O)N1CCCl	2442.1	Semi standard non polar	33892256
4-Hydroxyifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N1CCCl	2615.4	Semi standard non polar	33892256
4-Hydroxyifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N1CCCl	2549.9	Standard non polar	33892256
4-Hydroxyifosfamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CCOP(=O)(N(CCCl)[Si](C)(C)C(C)(C)C)N1CCCl	2965.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyifosfamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-4490000000-68b33a81b7ed61042169	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyifosfamide GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9477000000-c358b806368970e28e8a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyifosfamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 10V, Positive-QTOF	splash10-0a4i-9030000000-125f3622a612b6133e45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 20V, Positive-QTOF	splash10-001i-9100000000-2dc6532567c6dd55b170	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 40V, Positive-QTOF	splash10-0a4l-9000000000-ba299292144772f345bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 10V, Negative-QTOF	splash10-03fr-2790000000-5f30604369be13b4f4b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 20V, Negative-QTOF	splash10-0089-8900000000-4377372163ecc070ea4d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 40V, Negative-QTOF	splash10-002f-9000000000-1212b3cc3fd363e6eef8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 10V, Negative-QTOF	splash10-004i-0090000000-6c1af332aad878673a4b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 20V, Negative-QTOF	splash10-004i-0290000000-939a59c6fbceef5cc6af	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 40V, Negative-QTOF	splash10-00bi-3910000000-478bad8cbcb2e8e42d36	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 10V, Positive-QTOF	splash10-004i-0090000000-368a494088668b022c36	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 20V, Positive-QTOF	splash10-004i-2390000000-2745c533925b00075ccd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyifosfamide 40V, Positive-QTOF	splash10-03di-9300000000-1dd7c346907cc962b5f5	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Ifosfamide Action Pathway		Not Available
Ifosfamide Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

272429

KEGG Compound ID

C16553

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

308171

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kaijser GP, Ter Riet PG, de Kraker J, Bult A, Beijnen JH, Underberg WJ: Determination of 4-hydroxyifosfamide in biological matrices by high-performance liquid chromatography. J Pharm Biomed Anal. 1997 Mar;15(6):773-81. doi: 10.1016/s0731-7085(96)01893-6. [PubMed:9172103 ]
Kaijser GP, De Kraker J, Bult A, Underberg WJ, Beijnen JH: Pharmacokinetics of ifosfamide and some metabolites in children. Anticancer Res. 1998 May-Jun;18(3B):1941-9. [PubMed:9677448 ]

Showing metabocard for 4-Hydroxyifosfamide (HMDB0013861)

MOL for HMDB0013861 (4-Hydroxyifosfamide)

3D MOL for HMDB0013861 (4-Hydroxyifosfamide)

3D SDF for HMDB0013861 (4-Hydroxyifosfamide)

3D-SDF for HMDB0013861 (4-Hydroxyifosfamide)

PDB for HMDB0013861 (4-Hydroxyifosfamide)

3D PDB for HMDB0013861 (4-Hydroxyifosfamide)

SMILES for HMDB0013861 (4-Hydroxyifosfamide)

INCHI for HMDB0013861 (4-Hydroxyifosfamide)

Structure for HMDB0013861 (4-Hydroxyifosfamide)

3D Structure for HMDB0013861 (4-Hydroxyifosfamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra